Bissell's father served in the Marines during the Vietnam War, alongside author and journalist Philip Caputo. The two remained friends during Bissell's childhood and Caputo read Bissell's work and encouraged him in his early writing efforts.[3]

Bissell writes for Harper's Magazine, Slate, The New Republic,[4] and The Virginia Quarterly Review, where he is a contributing editor. While much of Bissell's magazine writing could be considered travel writing, his articles are more concerned with politics, history, and autobiography than tourism.[5]

As a journalist he traveled to Iraq[6] and Afghanistan during wartime.

Bissell's literary work has been recognized and highlighted at Michigan State University in their Michigan Writers Series.[7]

His book in collaboration with Jeff Alexander, Speak, Commentary, is a collection of fake DVD commentaries for popular films by political figures and pundits such as Noam Chomsky, Dinesh D'Souza and Ann Coulter.

His other books have won several prizes, including the Rome Prize, the Anna Akhmatova Prize, and the Best Travel Writing Award from Peace Corps Writers. His short stories and journalism have also been anthologized in The Best American Short Stories,The Best American Travel Writing, and The Best American Science Writing.[8] While much of Bissell's writing is concerned with issues of international relations and literary criticism, he frequently mentions Star Wars, J.R.R. Tolkien, and video games as well. The video game Gears of War 2, the first version of which Bissell wrote about for The New Yorker, contains a character named Hank Bissell, an apparent nod to him. In a March 2010 Observer article, he wrote about the appeal of games like Grand Theft Auto IV and his own simultaneous struggles with addiction to video games and cocaine.[9]

While Bissell has been critical of neo-conservatism, the Bush administration, and American unilateralism, his politics often do not fit within established categories of American liberalism and conservatism. Much of his work is concerned with the legacy of the Soviet Union and Communism.[11][12]